420964

(1S)-(+)-Ketopinic acid

99%

• Sinonimo/i: (1S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid
• Formula empirica (notazione di Hill): C₁₀H₁₄O₃
• Numero CAS: 40724-67-2
• Peso molecolare: 182.22
• Beilstein: 4180005
• Numero MDL: MFCD00168053
• Codice UNSPSC: 12352115
• ID PubChem: 24866367
• NACRES: NA.22

Proprietà

• Saggio: 99%
• Attività ottica: [α]23/D +58°, c = 1 in chloroform
• Punto di fusione: 237-239 °C (lit.)
• Gruppo funzionale: carboxylic acid; ketone
• Stringa SMILE: CC1(C)C2CCC1(C(O)=O)C(=O)C2
• InChI: 1S/C10H14O3/c1-9(2)6-3-4-10(9,8(12)13)7(11)5-6/h6H,3-5H2,1-2H3,(H,12,13)/t6-,10+/m1/s1; WDODWBQJVMBHCO-LDWIPMOCSA-N

Descrizione

Descrizione generale

(1S)-(+)-Ketopinic acid is a chiral ketone.[1]

Applicazioni

(1S)-(+)-Ketopinic acid may be used to prepare:

• Chiral phosphine-oxazoline ligands, which can used in asymmetric palladium-catalyzed Heck reaction of aryl or alkenyl triflates with cyclic alkenes.[1]
• A chiral imino-phosphine ligand, which can be used in palladium-catalyzed asymmetric Diels–Alder reactions to prepare six-membered carbocycles.[2]
• A chiral iminopyridine ligand, which can be used in copper-catalyzed Henry (nitro aldol) reaction between nitromethane and o-anisol to form the corresponding β-hydroxynitroalkane.[3]

Used to prepare a new chiral oxazolidone auxiliary[4] and a ketopinic derivatized polymer used for the deracemization of amines.[5] Starting material for the synthesis of homochiral 2,10-camphanediols.[6] Employed in the formation of a chiral Schiff base precursor to diethyl (S)-α-amino-α-alkyl phosphonates.[7]

Informazioni sulla sicurezza

• Pittogrammi: GHS07
• Avvertenze: Warning
• Indicazioni di pericolo: H315,H319,H335
• Consigli di prudenza: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Classi di pericolo: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Organi bersaglio: Respiratory system
• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Dispositivi di protezione individuale: dust mask type N95 (US), Eyeshields, Gloves